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WO2012020027A1 - Polyuréthanes stables à la lumière et leur utilisation - Google Patents

Polyuréthanes stables à la lumière et leur utilisation Download PDF

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Publication number
WO2012020027A1
WO2012020027A1 PCT/EP2011/063717 EP2011063717W WO2012020027A1 WO 2012020027 A1 WO2012020027 A1 WO 2012020027A1 EP 2011063717 W EP2011063717 W EP 2011063717W WO 2012020027 A1 WO2012020027 A1 WO 2012020027A1
Authority
WO
WIPO (PCT)
Prior art keywords
dimethyltin
catalysts
groups
component
catalyst
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2011/063717
Other languages
German (de)
English (en)
Inventor
Birgit Meyer Zu Berstenhorst
Uwe Pfeuffer
Norbert Eisen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Priority to US13/816,290 priority Critical patent/US20130165619A1/en
Priority to JP2013523597A priority patent/JP2013535559A/ja
Priority to CN2011800488700A priority patent/CN103189407A/zh
Priority to EP11745956.0A priority patent/EP2603538A1/fr
Publication of WO2012020027A1 publication Critical patent/WO2012020027A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2290/00—Compositions for creating anti-fogging
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the present invention relates to lightfast polyurethanes and their use.
  • PUR Polyurethanes
  • Moldings are therefore selected from aliphatic starting materials and, in the case of isocyanates, those compounds in which the NCO groups are not bonded directly to an aromatic group.
  • WO 2004/000905 uses such aliphatic isocyanates for the preparation of lightfast polyurethanes. It also addresses the problem of high volatile organic compound (VOC) levels, with peak levels of 250 ppm, preferably ⁇ 100 ppm, being required by the automotive industry for automotive interior applications.
  • VOC volatile organic compound
  • the solution used in WO 2004/000905 are incorporable catalysts having functional groups (-OH, -NH-, -NH 2 ) or high molecular weight catalysts, since the commercially available, non-incorporable bismuth and tin catalysts with alkyl ligands in which less than There are 13 carbons that increase VOCs.
  • the incorporable catalysts described in WO 2004/000905 are not commercially available.
  • Combinations of bismuth and tin catalysts are preferably used, with the bismuth catalyst used as the starting catalyst and the tin catalyst as the curing catalyst.
  • the object of the invention was therefore to produce a lightfast polyurethane (PUR) material which has low VOC values, can be quickly demoulded, can be stored for a few days and can be produced inexpensively.
  • the starting materials should be commercially available. To save costs, the components must be quickly demoldable. It is necessary that the reactive starting materials for the production of polyurethanes set quickly and already have a certain hardness when they are removed from the mold. On the other hand, however, a certain, not too short start time is needed to complete the tool completely. This should be "
  • the setting time should preferably not be less than 30 seconds.
  • the invention provides lightfast polyurethanes obtainable in the presence of e) catalysts and f) amine initiators by reacting a) one or more polyisocyanate components, where at least one polyisocyanate component contains at least 2 NCO groups which are not bonded directly to an aromatic group are, with b) one or more at least two compounds containing NCO groups reactive groups c) optionally chain extenders and / or crosslinking agents in the presence of d) optionally auxiliaries and / or additives, wherein as catalysts e) a combination of one or more Dimethyltin (IV) - dimercaptiden and one or more dimethyltin (IV) dicarboxylaten is used.
  • the catalyst combination is preferably used in an amount of 0.2 to 2 percent by weight, particularly preferably 0.4 to 1 percent by weight, based on the sum of components b), c), d), e) and f).
  • the molar ratio of dimethyltin (IV) dicarboxylates to dimethyltin (IV) dimercaptide is 99: 1 to 1: 1, preferably from 99: 1 to 3: 2, particularly preferably from 99: 1 to 5: 4.
  • dimethyltin dimercaptide preference is given to using catalysts from the group comprising dimethyltin (IV) didodecylmercaptide, dimethyltin (IV) bis (2-ethylhexylthioglycolate), dimethyltin (IV) dimethyleneisooctylestermercaptide and dimethyltin (IV) didecylmercaptide.
  • Preferred dimethyltin (IV) dicarboxylates are catalysts selected from the group consisting of dimethyltin (IV) butenyldicarboxylate, dimethyltin (IV) dilaurate and dimethyltin (IV) di (neodecylcarboxylate).
  • the polyurethanes according to the invention have starting times of> 20 seconds and setting times of> 30 seconds.
  • the starting time in the production of polyurethanes is the time which indicates the period from the mixing of the reaction components to the optically detectable reaction.
  • the setting time defines the time required from the mixing of the reaction components to the solidification of the surface. To complete a tool completely, the setting time should not be too small.
  • the curing of the material in the core is important in order to be able to demold easily, otherwise the component can warp.
  • the curing of the material is determined by means of the penetration measurement. This is determined with a penetrator (for example, the Cone Penetrometer H-4236 Humboldt) at 1400 g load and a rounded penetration tip with a diameter of 2.5 mm 60 seconds after mixing at room temperature, the penetration depth. Small values stand for a good through-cure, large values for a bad sales / through-hardening.
  • a penetrator for example, the Cone Penetrometer H-4236 Humboldt
  • a rapidly releasable polyurethane according to the invention should a) have a certain surface hardness, which is described by the setting time, and b) have a certain hardening after 1 minute, which is characterized by the penetration measurement.
  • the setting time should be between 30 and 50 seconds for good mold filling and fast mold release. Values between 1.8 and 10 mm are preferred as the pententration depths, with values of less than 3.5 mm being useful for very good mold release properties.
  • the polyurethane according to the invention preferably has a density of greater than 350 g / cm 3 .
  • the polyisocyanate component a) are organic isocyanate compounds having at least two
  • Another object of the invention is a process for the preparation of the lightfast polyurethanes according to the invention, which is characterized in that a) one or more polyisocyanate components, wherein at least one polyisocyanate component contains at least two NCO groups which are not directly bonded to an aromatic group , With ⁇
  • polyether polyols and / or polyester polyols and / or aliphatic oligocarbonate polyols having terminal OH groups, an average nominal functionality of 2 to 8 and an average equivalent weight of 100 to 4000, preferably 300 to 4000.
  • component c) are preferably 1 to 30 wt.%, Based on the weight of components b), c), d), e) and f), at least one compound used as functional groups only aliphatic or alicyclic OH groups , has a functionality of 2 to 8, a molecular weight of 62 to 500 g / mol and a content of primary OH groups of at least 50%.
  • component f) are preferably 1 to 10 wt.%, Based on the weight of components b), c), d), e) and f), at least one Amininitiatorkomponente forming a co-catalytic system with the catalyst component e) and 2 to 6 NH, NH 2 or OH functional aliphatic groups of which at least one group is a secondary or primary amino group and has an equivalent weight of at most up to 200.
  • Component e) used is a mixture of at least two dimethyltin (IV) catalysts, one catalyst preferably comprising at least one dimethyltin (IV) dimercaptide of the formula III and the second catalyst containing at least one dimethyltin (IV) dicarboxylate of the formula I or II is.
  • Pv2 linear or branched alkyl or alkenyl group having 1 to 19, preferably 1 to 13, particularly preferably 4 to 11 carbon atoms;
  • R 3 linear or branched alkylene or alkenylene group having 1 to 19, preferably 1 to 13, particularly preferably 1 to 5 carbon atoms;
  • R4 linear or branched alkyl or alkenyl group having 1 to 19 carbon atoms, optionally containing heteroatoms, such as. O, S, N, preferably with 2 to 14, particularly preferably with 4 to 14 carbon atoms.
  • the polyisocyanate component a) used is (c yclo) aliphatic polyisocyanates, preferably diisocyanates.
  • Suitable diisocyanates are any by phosgenation or by phosgene-free processes, for example by thermal urethane cleavage, accessible diisocyanates of the molecular weight range 140 to 400 with aliphatic or cycloaliphatic bound isocyanate groups, such as. B.
  • Isophorone diisocyanate (IPDI) and hexamethylene diisocyanate (HDI) are particularly suitable for preparing the polyurethanes according to the invention.
  • the isocyanates may be in the form of the pure compound or in modified form, for example in the form of Uretdiones, isocyanurates, allophanates, biurets, with Iminooxadiazindion- and / or Oxadiazin- trion Modell or in the form of urethane and isocyanate groups containing reaction products, so-called isocyanate prepolymers, and / or carbodiimide-modified isocyanates, are used.
  • the isocyanates a) preferably have an isocyanate content of 15 to 35 wt .-%.
  • Preferred but not exclusive isocyanate components are low viscosity products based on IPDI with a monomer content of 45 to 95 wt .-%, preferably 55 to 90 wt .-%.
  • the component b) preferably has an average hydroxyl functionality of 2 to 8 and preferably consists of at least one polyhydroxy polyether having an average molecular weight of from 1,000 to 15,000 g / mol, preferably from 2,000 to 13,000 g / mol and / or at least one polyhydroxy polyester having an average molecular weight from 1,000 to 10,000 g / mol, preferably from 1,200 to 8,000 g / mol and / or from at least one aliphatic oligocarbonate polyol having an average molecular weight of from 200 to 5000 g / mol, preferably from 400 to 1000 g / mol.
  • Suitable polyhydroxypolyethers are the alkoxylation products known per se from polyurethane chemistry of preferably di- or trifunctional starter molecules or mixtures of such starter molecules.
  • suitable starter molecules are water, ethylene glycol, diethylene glycol, propylene glycol, trimethylolpropane, glycerol and sorbitol.
  • Alkylene oxides used for the alkoxylation are, in particular, propylene oxide and ethylene oxide, these alkylene oxides being able to be used in any order and / or as a mixture.
  • Suitable polyester polyols are the per se known, hydroxyl-containing esterification products of preferably di- or trihydric alcohols, such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol and trimethylolpropane with underschüssigen amounts of preferably difunctional carboxylic acids, such as Succinic, adipic, phthalic, tetrahydrophthalic, hexahydrophthalic or mixtures of such acids.
  • di- or trihydric alcohols such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol and trimethylolpropane with underschüssigen amounts of preferably difunctional carboxylic acids, such as Succinic, adipic, phthalic, tetrahydrophthalic, hexahydr
  • Suitable aliphatic oligocarbonate polyols are the transesterification products of monomeric dialkyl carbonates known per se, e.g. Dimethyl carbonate, diethyl carbonate, etc., with polyols or mixtures of polyols having an OH functionality> 2.0, e.g.
  • the component c) is preferably difunctional chain extenders having a molecular weight of 62 to 500 g / mol, preferably 62 to 400 g / mol.
  • Preferred chain extenders c) include dihydric alcohols such as ethylene glycol, diethylene glycol, 1,4-butanediol, 1,6-hexanediol or mixtures of such diols.
  • chain extenders c) are preferably used in amounts of 1 to 30, preferably 2 to 15 wt .-%, based on the weight of components b), c), d), e) and f).
  • Component f) is an amine initiator component which forms a co-catalytic system with the catalyst component e) and preferably has 2 to 6 -NH, NH 2 or OH functional groups which are not directly attached to an aromatic group and at least one group of which has a secondary or primary amino group and an equivalent weight of at most up to 200.
  • Suitable amine initiators are described, for example, in EP 0929586 B1; furthermore, it is also possible to use Jeffamines.
  • the preferred amine initiators f) include diethanolamine, triethanolamine, ethanolamine, m-xylylenediamine, dimethylethanolamine and IPDA (isophoronediamine).
  • Component e) is a mixture of at least two dimethyltin (IV) catalysts, preference being given to at least one dimethyltin (IV) dimercaptide of the formula III and at least one dimethyltin (IV) dicarboxylate of the formula I or II.
  • Pv2 linear or branched alkyl or alkenyl group having 1 to 19, preferably 1 to 13, particularly preferably 4 to 11 carbon atoms
  • R 3 linear or branched alkylene or alkenylene group having 1 to 19, preferably 1 to 13, particularly preferably 1 to 5 carbon atoms
  • R4 linear or branched alkyl or alkenyl group having from 1 to 19 carbon atoms, optionally containing heteroatoms, e.g. O, S, N, preferably with 2 to 14, particularly preferably with 4 to 14 carbon atoms.
  • auxiliaries and additives d compounds of the type known per se can be used.
  • auxiliary agents and additives d the usual compounds, such as e.g. Stabilizers, blowing agents and in particular water are used, which may optionally be used in an amount of up to 0.3 wt .-%, based on the weight of components b), c), d), e) and f).
  • the preparation of the polyurethanes is carried out without added water.
  • the starting components are used in amounts such that an isocyanate index of 80 to 120, preferably 95 to 105, is obtained.
  • Isocyanate index is the ratio of the number of NCO groups to the number of reacting with the NCO groups multiplied by 100.
  • components b) to f) are generally combined to form a "polyol component B" which is then mixed with the polyisocyanate component and reacted, for example, in closed molds.
  • a polyol component B is then mixed with the polyisocyanate component and reacted, for example, in closed molds.
  • the temperature of the reaction components is generally within a temperature range of 20 to 60 ° C.
  • the temperature of the molds is generally 20 to 100 ° C.
  • the amount of material introduced into the mold is so dimensioned that bulk densities of the moldings of preferably 350 to 1100 kg / m 3 result.
  • the polyurethanes according to the invention are used, for example, for coating suitable substrates, for example metal, glass, wood or plastics. They are particularly suitable for the production of steering wheels, door side panels and instrument panel covers and decorative elements in the car interior.
  • Aliphatic polyisocyanate (from 70 wt .-% IPDI and 30 wt .-% IPDI isocyanurate) having an NCO content of 30.5 wt .-% and a viscosity of 200 mPas at 25 ° C.
  • Polyether polyol having an OH number of 28 prepared by alkoxylation of sorbitol with propylene oxide / ethylene oxide (PO / EO) in a weight ratio 82:18 and predominantly primary OH end groups.
  • F6 Fomrez UL 32 (CAS # 22205-30-7) from Momentive Performance Materials Inc., Germany; Dioctyltin (IV) didecylmercaptid
  • Isocyanate component a The amounts are given in the tables. The isocyanate index is 100 in each case.
  • Component e) is given as molar amount in mmol. By default, a total amount of substance of 1.5 mmol is used. For mixtures, the respective proportions are given in the tables.
  • the components b), c), e) and f) are successively weighed in a beaker and mixed. Subsequently, the isocyanate component a) is added and the entire system at room temperature for about 10 sec. With a Pendraulikrlicker at about 2500 U / min. stirred.
  • Example 1 Use of a single catalyst
  • the catalysts are used individually in an amount of 1.5 mmol.
  • VOC value [mg / kg]
  • the best combination is the catalyst combination E4 and E3 according to the invention, since both the setting times of less than 50 seconds and the penetration values are less than 3.5 mm. Compared to the sole use of the catalyst E4 can thus be achieved by combining with the catalyst E3 a higher activity at the same Monkatalysatorstoffmenge. Furthermore, even with non-installable catalysts, low VOC values of less than 100 ppm [mg / kg] can obviously be achieved.
  • the mixture tin (II) catalyst with dimethyltin (IV) di- (neo-decylcarboxylate) (Examples 3a to 3c) is first very active, the setting time is even a bit too short, but already after Hardly reacts for 4 days (penetration> 15 mm).
  • the system according to the invention with a dimethyltin (IV) dimercaptide and dimethyltin (IV) di (neo-decylcarboxylate) (Examples 3d-3f) likewise exhibits a good initial activity (penetration ⁇ 3.5 mm and good setting time in one manageable area), but hardly falls off.
  • the use of tin (II) catalysts in polyol compositions which must have a certain storage stability is discouraged.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des polyuréthanes stables à la lumière et leur utilisation.
PCT/EP2011/063717 2010-08-12 2011-08-09 Polyuréthanes stables à la lumière et leur utilisation Ceased WO2012020027A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US13/816,290 US20130165619A1 (en) 2010-08-12 2011-08-09 Light-fast polyurethanes and use thereof
JP2013523597A JP2013535559A (ja) 2010-08-12 2011-08-09 耐光性ポリウレタンおよびその使用
CN2011800488700A CN103189407A (zh) 2010-08-12 2011-08-09 耐光性聚氨酯及其用途
EP11745956.0A EP2603538A1 (fr) 2010-08-12 2011-08-09 Polyuréthanes stables à la lumière et leur utilisation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010039241.3 2010-08-12
DE102010039241 2010-08-12

Publications (1)

Publication Number Publication Date
WO2012020027A1 true WO2012020027A1 (fr) 2012-02-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/063717 Ceased WO2012020027A1 (fr) 2010-08-12 2011-08-09 Polyuréthanes stables à la lumière et leur utilisation

Country Status (5)

Country Link
US (1) US20130165619A1 (fr)
EP (1) EP2603538A1 (fr)
JP (1) JP2013535559A (fr)
CN (1) CN103189407A (fr)
WO (1) WO2012020027A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140131212A1 (en) * 2012-11-12 2014-05-15 Ppg Industries Ohio, Inc. Electrodepositable coating compositions containing dimethyl catalyst

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10208165B2 (en) * 2016-05-03 2019-02-19 Jerome Klosowski Curable silicone compositions that cure through command catalysis

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4242463A (en) 1979-12-19 1980-12-30 Sheller-Globe Corporation Color stable integral skin foam
EP0659792A2 (fr) * 1993-12-21 1995-06-28 Bayer Corporation Elastomères de polyuréthane aliphatiques obtenues par moulage réaction-injection
EP0929586B1 (fr) 1996-10-01 2001-04-18 Recticel Objets moules de polyurethanne elastomeres stables a la lumiere et leur procede de production
WO2004000905A1 (fr) 2002-06-21 2003-12-31 Recticel Materiau polyurethane photostable microcellulaire ou non cellulaire et procede permettant de le produire
EP1404740A2 (fr) 2001-06-27 2004-04-07 Bayer MaterialScience AG Procede de fabrication d'oligocarbonate diols aliphatiques
EP1518879A2 (fr) 2003-09-19 2005-03-30 Bayer MaterialScience AG Procédé pour la préparation de carbonatediols oligomériques et aliphatiques
EP1964866A2 (fr) * 2007-03-02 2008-09-03 Basf Se Fabrication de pièces de formage élastomères dures en polyuréthane
US20090082522A1 (en) * 2007-09-25 2009-03-26 Erickson John P Elastomeric composition

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4242463A (en) 1979-12-19 1980-12-30 Sheller-Globe Corporation Color stable integral skin foam
EP0659792A2 (fr) * 1993-12-21 1995-06-28 Bayer Corporation Elastomères de polyuréthane aliphatiques obtenues par moulage réaction-injection
EP0929586B1 (fr) 1996-10-01 2001-04-18 Recticel Objets moules de polyurethanne elastomeres stables a la lumiere et leur procede de production
EP1404740A2 (fr) 2001-06-27 2004-04-07 Bayer MaterialScience AG Procede de fabrication d'oligocarbonate diols aliphatiques
WO2004000905A1 (fr) 2002-06-21 2003-12-31 Recticel Materiau polyurethane photostable microcellulaire ou non cellulaire et procede permettant de le produire
EP1518879A2 (fr) 2003-09-19 2005-03-30 Bayer MaterialScience AG Procédé pour la préparation de carbonatediols oligomériques et aliphatiques
EP1964866A2 (fr) * 2007-03-02 2008-09-03 Basf Se Fabrication de pièces de formage élastomères dures en polyuréthane
US20090082522A1 (en) * 2007-09-25 2009-03-26 Erickson John P Elastomeric composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140131212A1 (en) * 2012-11-12 2014-05-15 Ppg Industries Ohio, Inc. Electrodepositable coating compositions containing dimethyl catalyst

Also Published As

Publication number Publication date
US20130165619A1 (en) 2013-06-27
CN103189407A (zh) 2013-07-03
EP2603538A1 (fr) 2013-06-19
JP2013535559A (ja) 2013-09-12

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